DE2306399A1 - 4,4'-DINAPHTHYL-1,1 ', 8,8'-TETRACARBONIC ACID DIIMIDE AS OPTICAL LIGHTENING AGENTS - Google Patents

Description

4,4'-Dinaphthyl-l, l ', 8,8'-tetracarboxylic acid diimides as optical brighteners

The present invention relates to new 4,4'-dinaphthyl-1, I ¹ , 8,8'-tetracarboxylic acid diimides, processes for their preparation and their use as optical brightening agents for organic materials.

The compounds according to the invention correspond to formula 1

309834/1130

R ° - Έ

R and R * tsaabtiäagig from each other
* a) hydrogen

b) alkyl of 2 to 18 carbons

c) Cycloalkyl containing 5 or 6 ring members . . . with 5 to 10 carbon atoms

d) alkyl of 1 to 18 carbon atoms substituted with hydroxy _s ,. Alkoxy substituted with 1 to 12 carbon atoms, optionally substituted with halogen or Sfethoxy _s Metbyl phenyl "carboxy, Carballcossy having 2 to 13 carbon atoms, optionally substituted on the nitrogen by alkyl having 1 to 12 CARBON '£ & t /: omeia. or phenyl-substituted carbamoy ^ ana optionally quaternized heterocycle with 5 or 6 ring members _s where 1 to 3 ring members represent nitrogen atoms _{s of} the sulfo group or its salts or optionally quaternized dialkylamine with 1 to 12 carbon atoms per alkyl part ₃ .0 iB 3 4/11 3.

e) optionally substituted with halogen, methyl or methpxy phenyl or

f) an optionally quaternized heterocycle with or 6 ring members, with 1 to 3 ring members nitrogen atoms represent,

X and X ¹ independently of one another, alkoxy with 1 to 4 carbon atoms in the 3- or 3'-position, or halogen,

Y and Y ¹ independently of one another in 6 or. 6'-position alkoxy with 1 to 4 carbon atoms, acyloxy with 1 to 4 carbon atoms, benzoyloxy or halogen,

t, u, ν and w independently of one another denote the number 1 or O and Z and Z ¹ independently of one another denote hydrogen or the sulfo group or their salts.

In the context of formula (1), the compounds of formula 2 are of particular interest - -

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R, and R, ¹ , independently of one another

a) hydrogen,

b) alkyl with 2 to 18 carbon atoms,

c) Cyclohexyl optionally substituted by methyl,

d) Phenylalkyl with 1 to 4 carbon atoms which is optionally substituted in the phenyl part with halogen, methyl or methoxy in the alkyl part,

e) with hydroxy, alkoxy with 1 to 12 carbon atoms or the sulfo group substituted alkyl with 2 to 4. ' Carbon atoms,

f) with a radical -COZ ₁ or -CON (Z ₂ Z ₃ ), where Z _{1 is} hydroxyl or alkoxy with 1 to 12 carbon atoms, Z «is hydrogen, alkyl with 1 to 4 carbon atoms or phenyl and Z« is hydrogen or alkyl with 1 represent up to 4 carbon atoms, substituted alkyl having 1 to 12 carbon atoms,

g) substituted with an optionally quaternized dialkylamine radical having 1 to 4 carbon atoms per alkyl part Alkyl with 2 to 6 carbon atoms,

h) alkyl having 2 to 4 carbon atoms, substituted by morpholino optionally substituted by methyl, Piperazino, piperidino, imidazolidon-1-yl or optionally in the 3-position with hydroxy or methoxy substituted pyridyl-2 or pyridyl. = 4, these

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nitrogen-containing radicals can be quaternized, i) optionally substituted with halogen, methyl or methoxy phenyl or
k) optionally quaternized pyridyl-2, pyridyl-4 or 1,2,4-triazol-3-yl and

X, X ¹ , Y, Y ¹ , Z, Z ¹ , t, u, ν and w have the meanings given above.

Of the compounds encompassed by the formulas (1) and '(2), the symmetrical ones deserve special attention (R = R ¹ or R ₁ = R ^, X = X ¹ , Y = Y ¹ , Z = Z', t = v and u = w), since they are generally more accessible.

Alkyl is to be understood as meaning both straight-chain and branched alkyl. Halogen stands in general for bromine or preferably chlorine. Acyloxy preferably represents acetyloxy.

Of the salts of the sulfonic acid group are the To emphasize alkali metal, alkaline earth metal, ammonium or amine salts. The alkali metal salts are preferred, especially the sodium salt.

Quaternized groups generally correspond to the sub-formulas

M or M

«F ³ . Q ©

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2306398

wherein M optionally substituted with hydroxy, or, alkoxy with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, optionally with chlorine or methoxy substituted benzyl or a radical -CH ₂ CN, -CKLCONH «or -CH ₂ COOR" where R "is is an alkyl group with 1 to 4 carbon atoms, and Q denotes halogen, such as iodine, bromine and preferably chlorine, an alkylsulfuric acid residue with 1 to 4 carbon atoms or a benzenesulfonic acid residue optionally substituted by methyl. As mentioned, the symmetrical connections are preferred. The compounds of formula 3 are of particular practical interest here

(3)

wherein Ro

a) hydrogen

b) alkyl of 2 to 12 carbon atoms

c) Cyclohexyl which is optionally substituted by methyl

d) Phenylalkyl with 1 to 4 carbon atoms in the alkyl part

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CfBA-GEIGYAG ■ 7 -

e) with hydroxy, alkoxy with 1 to 4 carbon atoms, carboxy *, carbalkoxy with 2 to 5 carbon atoms, the Sulfo group or an optionally quaternized dialkylamine radical with 1 to 4 carbon atoms per alkyl

. radical substituted alkyl with 2 or 3 carbon atoms

f) optionally quaternized morpholino, piperazino, imidazolidon-1-yl, pyridyl-2- or 3-hydroxypyridyl-2-ethyl

g) methoxyphenyl or phenyl or ^! h) optionally quaternized pyridyl-2, pyridyl-4 or 1,2,4-triazol-3-yl,

X, hydrogen, or in the 3- or 6-position, or 3 ¹ - or 6-position befindliches alkoxy having 1 to 4 carbon atoms or chlorine, and

Z is hydrogen or the sulfo group or their salts,
and especially the compounds of formula 4

(4)

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• a) Alkyl with 2 to 12 carbon atoms

b) substituted with alkoxy having 1 to 4 carbon atoms Alkyl with 2 or 3 carbon atoms,

c) substituted with carbaikoxy having 2 to 5 carbon atoms Alkyl with 1 to 11 carbon atoms,

d) with diaikylamino with 1 to 4 carbon atoms per alkyl part substituted alkyl of 2 to 6 carbon atoms or

e) pyridyl-2 or 3-hydroxypyridyl-2 and! X ₁ denotes hydrogen or alkoxy with 1 to 4 carbon atoms or chlorine in the 3- or 6-, or 3'- or 6'-position.

In the meaning of alkyl with 2 to 18 or 2 to 12 carbon atoms for R, R ¹ , R 1, R 1, R 1 or Ro, branched alkyl with 3 to 18 or 3 to 12 carbon atoms is preferred.

The compounds of the formulas (1) to (4) are prepared analogously to processes known per se.

One mole of a compound is used to prepare a compound of the formula (1) or of a subordinate form of formula 5

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CIBA-GEIGYAG

(5)

wherein the various symbols have the meanings given, with one mole each of a compound of the formulas 6a and 6b

(6a) R-NH ₂

and

R '-NH,

(6b)

wherein R and R ', with the exception of the quaternizing groups, have the meaning given to.

Symmetrical compounds, for example those of the formula (3), are produced by reacting a compound of formula 7

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(7)

CIBA-GEIGYAQ - 10 -

wherein X- ^ has the meaning given, with a compound of formula 8

R ₁ -NH ₂ (8),

where R is the specified with the exception of the quaternization groups Has meaning in a molar ratio of 1: 2.

The mere reactants can be added together for this condensation. However, it is advantageous to carry out the process in solvents which are inert towards the reactants. Examples are organic solvents such as aromatic hydrocarbons and chlorinated hydrocarbons, for example toluene, xylene, chlorobenzene, dichlorobenzene, alcohols, for example isopropanol, butanol, glycols such as ethylene glycol, glycol ethers, dimethylformamide. Some reactions can also be carried out in the aqueous phase. The reaction temperature depends on the type of components to be reacted, in virtually eligible cases, it is between 40 and 200 ⁰ C. One can apply the reactants in stoichiometric amounts, an over- or under-shot jedoch'ist in some cases of a or another reaction partner advantageous.

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In general, one works with an excess of amine compound, one dinaphthyltetracarboxylic acid anhydride per mole 2 to 8, preferably 2 to 3 moles of amine compound are added.

Contain the compounds according to the invention
Sulpho groups, such groups can be introduced in the usual way by subsequent sulphonation, for example with oleum. Compounds according to the invention which contain quaternizable nitrogen atoms can likewise be quaternized by likewise customary processes.

These. Quaternization can, in an inert solvent for the reactants, at temperatures from 0 to 200 ⁰ C, preferably carried out at 20 to 150 ⁰ C.
will. Such solvents are, for example, aromatic hydrocarbons such as benzene, toluene and xylene; Halogenated hydrocarbons such as methylene chloride, tetrachlorethylene, chlorobenzene, bromobenzene or dichlorobenzene, also
also nitrobenzene, lower alkanols and open or cyclic ethers, such as ethanol, isopropanol, butanol, diethyl ether, dibutyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, tetrahydrofuran or dioxane; lower ketones such as acetone or methyl ethyl ketone; Fatty acid amides such as dimethylformamide or dimethyl acetamide; SuIf oxy de such as dimethyl sulfoxide and ureas such as tetramethylurea. If desired, the resulting quadratic

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natural salts can be converted into other salts by double conversion.

The reaction described above can in principle be carried out with any quaternizing agent. For example, such quaternizing agents are alkyl halides such as methyl iodide, butyl bromide, dialkyl sulfates such as Dimethyl sulfate, diethyl sulfate, aralkyl halides such as Benzylch.lor.id or bromide, haloacetic acid ester and their derivatives, esters of benzenesulfonic acid or p-toluenesulfonic acid, in particular their methyl or ethyl esters.

The 4,4'-dinaphthyl-1,1 ', 8,8'-tetracarboxylic anhydrides used as starting materials of formula (5) or (7) can by condensation of the corresponding 4-bromo-naphthalic acid with copper powder in one inert organic solvent can be obtained according to Ulimann.

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- is - 2306393

■. . The new compounds defined above show a more or less pronounced fluorescence in the dissolved or finely divided state. They can be used for the optical brightening of a wide variety of synthetic, semi-synthetic or natural organic materials or substances which contain such organic materials. '. · _ - .-. -, '-

■ '■ - this purpose include for example, without having to be expressed by the following overview any limitation, the following groups of organic materials, insofar as optical brightening thereof would be considered, include: · - -. ■

I. ": Synthetic organic high molecular materials:

a) Polymerization products based on organic compounds containing at least one polymerizable carbon-carbon double bond, ie their homopolymers or copolymers and their aftertreatment products such as crosslinking, grafting or degradation products, polymer blends or by modifying reactive groups products obtained, for example polymers based on ct., ß-unsaturated carboxylic acids or derivatives of such carboxylic acids, in particular of acrylic compounds (such as acrylic esters, acrylic acid, acrylonitrile, acrylamides and their derivatives or their methacrylic analogs), of olefin

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'. Hydrocarbons (such as ethylene, propylene., Styrenes or dienes, also so-called ABS polymers), poly-

. merizates based on vinyl and vinylidene compounds (such as vinyl chloride, vinyl alcohol, vinylidene chloride),

". b) Polymerization products obtainable by ring opening, for example polyamides of the polycaprolaetam type, furthermore Polymers that use both polyaddition and

. ' -Polycondensation are available, such as polyethers or polyacetals, /; ■ '· ";.' - -.". -. -

c) ".. ■ polycondensation products or precondensates ... based on bi- or polyfunctional compounds with condensable Groups whose homo- una mixed condensation products and post-treatment products, such as * ■ -. wise polyesters, especially saturated (e.g. ethylene

■ glycol terephthalic acid polyester) or "unsaturated (e.g. maleic acid dialcohol polycondensates and their crosslinking

products with polymerizable vinyl monomers), unbranched as well as branched (also based on higher quality Alko-'i holly, such as alkyd resins), polyesters, polyamides (e.g. hexa- • methylenediamine adipate), maleinate resins, melamine resins, their Precondensates and analogues, polycarbonates, silicones,

■ d); Polyaddition products such as polyurethanes (crosslinked and uncrosslinked), epoxy resins. '.

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- 15 -

II. "Semi-synthetic organic materials, e.g. Cellulose esters of various degrees of esterification (so-

"narintes 2 l / 2-acetate, triacetate) or cellulose ether, .regenerated cellulose (viscose, copper ammonia cellulose) or their aftertreatment products, casein plastics. ; .., - - ν:, ■ · ■ ;. ":. · ..J ^

III. .Natural organic materials animalistic . or of vegetable origin, for example based on

.. of cellulose or proteins such as cotton, wool, linen, silk, natural lacquer resins, starch, casein. : ': · - _: - ·. The organic materials to be optically brightened can be used in a wide variety of processing states (raw materials, semi-finished products or finished products).

■ hear. On the other hand, they can be in the form of

. most shaped structures exist, i.e., for example, as predominantly three-dimensionally extended bodies such as plates, Profiles, injection moldings, various types of " pieces, schnitzel, granules or foams, also as

'. predominantly two-dimensional bodies such as films, foils, lacquers, coatings, impregnations and coatings or as predominantly one-dimensional bodies such as threads, fibers, flakes, wires. The said materials can on the other hand also in unformed states in the various homogeneous or inhomogeneous distribution

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ciBA-GEiGYAG - Ib -

■ shapes, e.g. as powders, solutions, emulsions, dispersions, Latices, pastes or waxes are present.

Fiber materials can be, for example, as endless threads (drawn or undrawn). Staple fibers, flakes, hank goods, textile threads, yarns, twisted threads, fiber fleeces, felts, wadding, fleece structures or as textile fabrics or textile composites, knitted fabrics and as papers, cardboard or paper pulps. _v ""

The new compounds of the formulas (1) to (4) are important for the treatment of organic textiles Materials, in particular textile fabrics. If fibers, which as staple fibers or filaments, can be in the form of strands, woven fabrics, knitted fabrics, nonwovens, flocked substrates or composites, with the compounds according to the invention are to be optically brightened, this is advantageously done in an aqueous medium in which the compounds in question in finely divided form (suspensions, so-called microdispersions, if appropriate Solutions) are available. If appropriate, dispersing, stabilizing, wetting and other agents can be used during the treatment Auxiliaries are added.

Depending on the type of brightener compound used, it may be beneficial to use neutral or alkaline or acidic baths. The treatment is usually carried out at temperatures of about

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to 14O ° C, for example at the boiling point of the bath or in the vicinity (about 90 ⁰ C) carried out. Solutions or emulsions in organic solvents can also be used for the finishing of textile substrates, as is practiced in dyeing practice in so-called solvent dyeing (padding thermofixing application, exhaust dyeing process in dyeing machines).

·.: ... .- The new optical brightening agents .according to the present Invention can furthermore be added to or incorporated into the materials before or during their "pre-forming". For example, they can be used in the production of films, foils (e.g. rolling in polyvinyl chloride in the Add heat) or moldings to the molding compound or injection molding compound.

If the shaping of fully or semi-synthetic organic materials by spinning processes or spinning masses takes place, the optical brighteners can be applied using the following methods:.

Addition to the starting substances (e.g. monomers) or '■ intermediate products (e.g. precondensates, prepolymers), i.e. before or during the polymerization, polycondensation or polyaddition, .. "* * - '■' · powdering on polymer chips or granulates for spinning masses, ■ - '..' »■ ·.

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. ■ -._ ■ Bath coloring of polymer chips or "granules" • 'for spinning masses,; "■ ·.-.- · -

Dosed. Addition to spinning melts or spinning solutions, r. Application on tow before stretching.

'· ■■■■' ■ "" The new optical brightening agents according to this one Invention can also be used, for example, in the following forms of use:. "- - '' ■ 'a) . "Mixtures with dyes (nuances)"

• or pigments (coloring or especially e.g. white pigments) or as an additive to dye baths, printing, etching or

. Reserve pastes *. Also for the aftertreatment of dyeings, prints or etching, " ^: ■ · ^: ..-.'- · ■ - '"

-.b) "" in mixtures with so-called "carriers", Netz-r agents, plasticizers, swelling agents, antioxidants, light protection agents, Heat stabilizers, "chemical bleaching agents

: teln (chlorite bleach, bleaching bath additives), ""

. c) in a mixture with crosslinkers, finishing agents (e.g. Starch or synthetic finishes) as well as in combination

. with a wide variety of textile finishing processes, in particular Synthetic resin finishes (e.g. anti-crease finishes v / ie "wash-and-v / ear", "permanent-press", "no-iron"), furthermore Flame-resistant, welch-grip, dirt removal ("anti-soiling") - boring Antistatic or antimicrobial equipment

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d). Incorporation of the optical brightening agents into polymers Carrier materials (polymerization, polycondensation or polyaddition products) in dissolved or dispersed form for use e.g. in coating, Impregnating agents or binders (solutions, dispersions, Emulsions) for textiles, fleece, paper, leather,

e) as additives to so-called "master batches",

f) 'as additions to the most diverse industrial Products to make them more marketable (e.g. aspect improvement of soaps, detergents, pigments,

g) in combination with other, optically brightening substances, ■ ... " ^: ."":.'..:' ... · -

h) in spinning bath preparations, i.e. as additives to spinning baths, such as those used to improve lubricity for the further processing of synthesis »fibers are used, or from a special bath before stretching Fiber,;

i) as scintillators, for various purposes of the photographic type, e.g. for electrophotographic reproduction or supersensitization for the optical brightening of photographic layers, optionally in combination with white pigments such as TiO _2.

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■ or ennobling methods combined, the combined

Treatment in many cases is advantageous with the help of suitable permanent preparations, polygamy

Contain optically brightening compounds in such a concentration that the desired brightening effect is achieved will. > ·. · .-. · -..- ·. ". - ·" \. ·

'In certain cases the brighteners will go through a follow-up treatment brought its full effect. This can for example a chemical (e.g. acid treatment), a thermal (e.g. heat) or a combined chemical / thermal

represent mixed treatment. This is how you do - for example - ■ wise in the optical brightening of a number of fiber substrates., e.g. of polyester fibers, with the inventive Brightening appropriately "in such a way that one can do this "Fibers with the aqueous dispersions (possibly also

• Solutions) of the brightening agents at temperatures below 75 C, e.g. at room temperature, impregnated and "a dry heat

'. treatment is subjected at temperatures above 100 C, wherein I is recommended generally that fiber material .noch to dry before at moderately elevated temperature, eg · be "l at least 60 ° C to about 150 ⁰ C. -The Wärmebehandlung.in

The dry state is then advantageously carried out at temperatures between 120 and 225 C, for example by heating in a drying chamber, by ironing in the specified temperature range or by treating with dry, superheated steam. The drying and dry heat treatment can also be carried out immediately one after the other

'' 30 98 34/1 1 * 3 0.

or can be combined in a single operation.

The amount of new optical brighteners to be used, based on the material to be optically brightened, can vary within wide limits. Even with very little. Quantities, in certain cases e.g. those of 0.0005 percent by weight, a clearer and more durable effect can be achieved. However, quantities of up to about 0.8 percent by weight can also be used and optionally up to about 2 percent by weight are used. For most practical purposes are preferably amounts between 0.005 and 0.5 percent by weight of interest.

The new optical brightening agents, provided they contain water-solubilizing groups, are also particularly suitable as additives for washing baths or for commercial and household detergents, and they can be added in various ways. They are expediently added to washing baths in the form of their solutions in aqueous or organic solvents or also in finely divided form as aqueous dispersions. They are advantageously added to household or commercial detergents in any phase of the detergent production process, for example the so-called "slurry" before atomization of the washing powder or when preparing liquid detergent combinations. The addition can take place either in the form of a solution or dispersion in water or other solvents or, without auxiliaries, as a dry brightener powder. You can

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"brighteners, for example, with the detergent substances mix, knead or grind and so the finished Mix in washing powder. However, they can also be dissolved or "predispersed" and sprayed onto the finished detergent will. . ·; ■ - ·· ..-. '"" .. / ·

• The known mixtures are used as detergents of washing active substances such as soap in the form of chips and powder, synthetics, soluble salts of.

• ·. * - ■ ■ · - * / Sulfonic acid half-esters of higher fatty alcohols., Higher and / or

'. polyalkyl-substituted arylsulfonic acids, sulfocarboxylic acid esters; medium to higher alcohols, fatty acid acylaminoalkyl or aminoaryl glycerol sulfonates, phosphoric acid esters of fatty alcohols in fraction. As a construction material. so- '· -.

.'Called "Builders", come Z = B. Alkali poly- and polymetaphosphates, Alkali pyrophosphates, alkali salts of carboxymethyl cellulose and other 'Feoil redepositioninhibitors', furthermore

. Alkali silicates., Alkali carbonates, alkali borates, alkali perborates, Nitrilotriacetic acid, ethylenediaminotetraacetic acid, foam stabilizers such as alkanolamides of higher fatty acids

- '. acids, into consideration. Furthermore, in the detergents, for example be included: -. - "-.. ' ■ "'" ■ ".

■ - · antistatic agents, moisturizing skin protection agents such as lanolin, enzymes, antimicrobials, perfumes and dyes. '' ·. . .: ■ · ■ - * ■ -

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The new optical brighteners have something special. The advantage that they can also be used in the presence of active chlorine donors., such as hypochlorite, are effective and without significant loss of the effects in washing baths with non-ionic detergents, e.g., alkyl phenol polyglycol ethers can be used. . "" .- · '

• .- ■ The compounds according to the invention are used in quantities from 0.005 - l / pounds or more, based on the weight of the liquid liquid or powdered ready-to-use detergent added. : YJash liquors that contain the specified amounts of the claimed * Contain optical brighteners, give when washing textiles made of cellulose fibers, polyamide fibers, highly refined. ten cellulose fibers, polyester fibers, full a brilliant aspect in daylight. -. · -.

_; The washing treatment is carried out, for example, as follows:. · '. . ^:

The specified textiles are used for 1 to 50 Treated minutes at 20 to 100 C in a washing bath containing 1 to 10 g / kg of a built-up, composite detergent 'and $ 0.05 to $ 1 based on detergent weight claimed Contains lightening agents. The liquor ratio can be 1: 3 to 1:50. After washing, rinse as usual and dried. The VJaschbad can be used as bleach additive 0.2 g / l active chlorine (e.g. as hypochlorite) or 0.1 to 2 g / l Contain sodium perborate. .

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In the. Examples are parts, if not otherwise stated., always parts by weight and percentages always Weight percent. Unless otherwise noted, melting and boiling points are uncorrected. The temperatures are given in degrees Celsius. '

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-25-2305399

example 1

19.71 g of finely ground 4,4'-dinapthtyl-l, .l ', 8.8 ^! ~ TetracarbonsMuredianhydrid are suspended in 300 ml of water and mixed with 36.5 g of isobutylamine. The suspension is then stirred for 18 hours at room temperature, a solution being formed after about 2 hours. It is then heated to 95-100 ° for 5 hours. After cooling, the precipitated product is filtered off, washed with water and dried at 100 in vacuo. The yield is 23.8 g.

After repeated recrystallization from benzene, with the aid of fuller's earth, 21.2 g of the compound are the Formula 9 -

P (9)

-CH ₀ -CH ²

/ CH

obtained as a white powder with a melting point of 217 to 218 ° C. That Product can be dissolved in chlorobenzene with blue-violet fluorescence. The new connection is very suitable for Lightening of various organic polymeric substances, especially synthetic textile fibers and polymers

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Plastics.

The compounds of the formula (10) listed in Table I are prepared in an analogous manner. You x ^ iron similar properties to the product mentioned above.

R-N V = ^

- R

(10)

Table I.

formula R. ,-H Focal point
incorr, in ⁰ C (H) -C ₂ H ₅ over 300 ° (12) -nC ₃ H ₇ . Over 300 ° (13) ^ nC ₄ H ₉ 298-299 ° (14) -IsO-C ₃ H ₇ 194-196 ° (15) -GH ₂ CH ₂ OH 282-284 ° (16) - (CH ₉ ) O-OCHo; 248-2S0 ⁰ (17) 215-217 °

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Example 2

19.71 g of finely ground 4,4 '~ dinaphthyl-l, l ^l, 8,8'-tetracarboxylic dianhydride are added in 250 ml of ethylene glycol uad slurried with 14.12 g of 2-aminopyridine. The suspension is heated to 140 within 3 hours and stirred at this temperature for 4 hours. After cooling, the precipitated product is filtered off, washed with ethanol and dried at 100 in a vacuum. The yield is 26 g.

After several times. Recrystallization from chlorobenzene, with the aid of fuller's earth, 23.7 g, corresponding to 88 % of theory, of the compound of formula (18) as a white powder of Smt>. received over 260.

(18)

The product dissolves in chlorobenzene with a blue-violet color Fluorescence. The new compound is an excellent means of lightening plastics and synthetic fibers.

In an analogous manner are those listed in Table II Compounds of formula (19) prepared.

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They have similar properties to the product mentioned above.

R-N V =

(19)

Table II

formula R. Melting point
incorr. in ° C (20) - (CH ₂ ) ₃ COOH 175-177 ° (21) - (CH ₂ ) ₅ COOH 114-116 ° (22) - (CH _o ) _in C00H
Z IU 111-112 °. (23) -CH ₂ -COOH over 260 ° (24) ¹ O ' Over 260 ° H (25) -CH ₂ CH ₂ -SO ₃ H over 260 ° (26) Over 260 ° (27) - -CH ₂ CH ₂ -COOH _: , About 260 ° (28) ■ - (CH ₉ ) ₉ -NH NH
* · * · Ν .. .J 229-23'l ^o

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CLBA-GEIGY AG Example 3

19.71 g of finely ground 4,4'-dinaphthyl-1,1 ¹ -8,8'-tetracarboxylic dianhydride are heated to 160 with 250 ml of 1,2-dichlorobenzene and 19.4 g of n-octylamine within 3 hours and for more stirred for two hours at this temperature. The resulting solution is filtered while hot and the 1,2-dichlorobenzene is distilled with steam. The product that remains is filtered off with suction and dried at 100 in a vacuum. The yield is 30.1 g, corresponding to 97.5 70 of theory.

After repeated recrystallization from toluene, with the aid of fuller's earth, 23.9 g, corresponding to 77.5 % of theory, of the compound of the formula 29

obtained as a light beige powder with a melting point of 157 to 159 ° C. '

Those listed in Table III are shown in an analogous manner Compounds of formula (30) prepared.

RH
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JT y O V Λ \ _ ~ v Λ J

CIBA-GEIGY AG

> 30 _

■ table. III

formula R - ". ■ 0 . Melting point ~
inaccurate in C (31) " - (CH ₂ , ^ ■ - _{H c} 139-141 '(32;) -/ H\ 174 - Ϊ75 (33) . > 3 "198-200 (34.) 221-222 (35) / - \ 261-264 • (36) CH_ "" over 26O (37) 0 -CH- ^ \ over 26O (38) π υ Ö Π Ö Q * 3 /
2 5 * over 26O (3-9) over 26O ' - (40). 274-275 (41) 265-267 (42? 240-243 / 1130.

CIBA-GEIGYAG Example 4

19.7 g of 4,4'-dinaphthyl-1,1 ', 8,8'-tetracarboxylic acid dianhydride are heated to 100 with 130 ml of dimethylformamide. A solution of 10.2 g of aniline in
Pour in 20 ml of dimethylformamide. It is stirred for a further 2 hours at 100 and then heated to boiling for 5 hours. Colorless crystals precipitate over the course of the hours from the solution that has formed after a short time.
It is allowed to cool to 80 and the precipitated product is filtered off. It is made with dimethylformamide and alcohol
washed and dried at 120 ° in vacuo. The yield is 22.8 g. After recrystallization from nitrobenzene, 20.5 g of the compound of the formula (43) are obtained.

(43)

The melting point is higher than 330 °. The compound of the formula (44), melting point above 300 ^° C., is prepared in an analogous manner,

(44)

OCH

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Example 5

18.2 g of finely ground 4,4'-dinaphthyl-3,3'-dimethoxy-1,1 ', 8,8'-tetracarbic dianhydride are suspended in 500 g of water and with 35.5 g of a 50.7% aqueous ethylamine solution offset. The suspension is stirred for 18 hours at room temperature. Then you heat for one Hour to 5-60 and then, to complete the reaction, another 6 hours to 90-95. After cooling down the precipitated product is filtered off, with • Washed water and dried at 120 ° in a vacuum. the Yield is 1.9.4 g.

After repeated recrystallization from chlorobenzene (under With the help of fuller's earth) the compound of formula 45 -. .

H ₅ C-CH ₂ -

(45)

N-CH ₂ -CH ₅

as pale yellow crystals with a melting point of 292 to 293 ° C . obtain.

30 9834/1130

CIBA-GEIGY AG

Example 6

18.2 g of 4,4'-dinaphthyl-6,6 ^f ~ dimethoxy-l, l ^f , 8,8'-tetracarboxylic dianhydride are made up with 320 g of 1,2-dichlorobenzene and 14.2 g of n-propylamine for one hour 60 - 70 heated. The mixture is then heated to 110 and stirred at this temperature for a further hour. To complete the reaction, the mixture is heated to 170-180 for another hour. The resulting solution is filtered while hot and the 1,2-dichlorobenzene is distilled off in vacuo. After repeated recrystallization from chlorobenzene with the aid of fuller's earth, the compound of formula 46 is obtained

(46)

as pale yellow crystals with a melting point of 234 to 235 ° C obtain.

Example 7

11.2 g of the compound of the formula (12) are introduced into 50 ml of 25.7% oleum. The mixture is now within one hour heated to 90 and stirred for 4 hours at this temperature. After cooling down, the clear,

309834/1130

CIBA-GEIGY AG

poured dark brown solution onto 700 g of ice and added of sodium chloride salted out the disulfonic acid. The yellow precipitate is filtered off with suction, washed with brine and with 100 dried in vacuo. After recrystallization, 14.8 g, corresponding to 88% of theory, of the compound of Formula 47 -

(47)

as a yellow powder with an absorption of O 358 nm obtain.

Similarly, using it accordingly subs tuier ter 4,4'-Dinaphthyl-1,1 ', 8, 8'-tetracarbons a'ur ediamide, the compounds listed in Table IV below are produced »

(48)

309834/1130

ciBA-GEiGYAG - 35 -

Table IV

formula R. ^Λ . nm Max - (49) -HC ₄ H ₉ 360 (50) -CH ₂ CH ₂ -OH 359 (51) - (CH ₂ ) ₃ -OCH ₃ 361 (52) -CH ₂ CH ₂ -COOH 358

Example 8

11.6 g of finely ground sodium salt of 4,4'-dinaphthyl-l, 1 ', 8,8'-tetracarboxylic acid diamide-N, N'-dipropionic acid together with 4.62 g of anhydrous sodium carbonate and 5.56 g of dimethyl sulfate in 100 ml of chlorobenzene stirred at 100 ° for 24 hours. The reaction mixture is cooled, suction filtered and the filter material is washed out thoroughly with water. The remaining product is recrystallized twice from chlorobenzene with the aid of fuller's earth. 9 g, corresponding to 80 7 _O of theory, of the compound of the formula 53 are obtained

(53) OLOOC-CHgOIg-r " ^x - '

N-OI CH ₂ -COOCH

as a white powder with a melting point of 254 to 256 °.

309834/1130

ciBA-GEiGYAG _ 36 -

Those listed in Table V are listed in an analogous manner Compounds of formula (54) prepared. They have similar properties to the product mentioned above on. ■

O / / '
I. ) 0
<
NO
/ O ^ < V Tabel- >

(54)

formula R. Melting point ■ (55) - (CH ₂ ) ₃ COOCH ₃ 205-206 ° (56) - (CH ₂ ) ₅ COOCH ₃ 167-169 ° (57) -CH ₂ -COOCH ₃ over 260 ° (58) - (CH _o ) _in C00CH _o
i. 10 y 108-109 °

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ciBA-GEiGYAG "37 -

Example 9

_16: g of 4,4'-binaphthyl-1,1 ', 8,8'-tetracarboxylic acid-N, N' - (2-dimethylaminoethyl) diimide (formula (34) in 150 ml of chlorobenzene at 100 ⁰ C under. 8.2 g of dimethyl sulfate were added to the stirring, the mixture was stirred at 100 ° for 2 hours and then cooled, the white precipitate formed was filtered off, washed with hot chlorobenzene and dried in vacuo at 100. This gave 23 g, corresponding to 97.5 ° L the theory, the compound of formula (59)

• 2 CH SO ^

> - \ y ~ {x-4

with a melting point above 300.

The new compound dissolves in water with blue fluorescence and is very suitable for lightening polyacrylic fibers.

309834/1130

OBA-GEIGYAG

In an analogous manner, those in the table below compounds of the formula (60) listed. They have properties similar to the above Product on. '"T"'

062)

(.63) (64)

(65)

Table VI

-CPLCH, .- NHO
^{2 2} | \ /

-CSI.

CH ₃ SO ₄

CH ₃ SO ₄

Cl 'ZnCl, cH ^ ao.,

■■ -τ 3 4

309834/1

CLBA-GEIGY AG

Example 10

0.12 ml of 85% formic acid are added to 100 ml of water, and additionally given 0.06 g of alkyl polyglycol ether.

A solution is prepared from the optical brightener of the formula (55) by dissolving 1 g in 1000 ml of water. from 1.5 ml of this stock solution are added to the solution described above. This aqueous solution containing the brightener is heated to 60 C. Then a 3 g heavy Orion fabric is placed in the solution. The temperature is raised within 10 - 15 minutes to 95 - 98 C and left at this temperature for 60 minutes. The tissue is then 2 minutes Rinsed in running cold water and then dried at 60 ° C. for 20 minutes.

The fabric treated in this way shows a clear lightening effect.

If, instead of the above-mentioned brightener, equal amounts of a brightener of the formulas (33), (34), (35), (36), (61), (62), (63), (64). Or (65), one obtains with otherwise the same working method, similar effects.

Example 11

0.06 ml of acetic acid 40 7 _o ig and 0.06 ml are added to 95 ml of water

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CIBA-GEIGY AG

- .4D _

Given alkyl polyglycol ether.

An optical brightener of the formula- (9) becomes a Solution prepared by dissolving Ig in 1000 ml DMF. 6 ml of this stock solution are added to the one described above Solution. This aqueous dispersion containing the brightener is heated to 60 ° C., then a 3 g heavy triacetate fabric into the solution. ! The temperature is increased within 10 - 15 minutes to: 95 - 98 C and left at this temperature for 30 minutes. The fabric is then rinsed for 2 minutes in running, cold water and then dried at 60 ° C. for 20 minutes.

The fabric treated in this way shows a clear lightening effect. '

If, instead of the above-mentioned brightener, equal amounts of a brightener of the formulas (12), (14), (16), (29), or (31), one obtains with otherwise the same method of operation similar effects.

Example 12 ^:

, 0.06 g of an alkyl polyglycol ether are added to 100 ml of water ; given. From the optical brightener of the formula (9)

a solution is made by mixing 1 g in 1000 ml Dimethylformamide dissolves. From this stock solution one gives 1.5 ml to the aqueous solution described above.

30 98 34/1130

CIBA-GEIGY AG

- ⁴¹ -. 2306393

'This aqueous solution containing the brightener is on Heated at 60 ° C., a 3 g nylon pile fabric is then added into the solution. The temperature is increased internally

; 10-15 minutes to 90 - 92 ° C and leaves at this Temperature 30 minutes. The fabric shows a white and brilliant appearance. .

If, instead of the above-mentioned brightener, equal amounts of a brightener of the formulas (12), (13), (14), (25), (29), (AO), (41) or (47), one obtains with otherwise " similar effects in the same way of working.

[ Example 13

From the optical brightener of formula ( '9) is produced an approximately 10 7oige dispersion, sand milling with 1000 ml of water diluted and added 2 g of wetting agent by mixing 100 g. "With this dispersion (20 ⁰ C) is padded to a polyester fabric (Squeeze effect 50 - 60%, roller pressure

'.O

• 30 kg / env, speed 3m / min.) · The fabric is Dried at 60 ° C for 20 minutes.

The dry tissue is then treated for 30 seconds : Fixed at 200 ° C.

treated fabric shows a clear brightening «« f € ect

309834 / 113-0

CfBA-GEIGYAG.

If, instead of the abovementioned brightener, the same amounts of a brightener of the formulas (12), (13), (14), (3-8), (29), (40), (42) or (45) are obtained, at otherwise the same working method, similar effects. ·. '

Example 14

0.06 g of 40% acetic acid and 0.06 g are added to 100 ml of water Given alkyl polyglycol ether.

From the,. optical brightener of the formula (.9), a solution is prepared by dissolving 1 g in 1000 ml of DMF. 1.5 ml of this stock solution is added to the solution described above. This aqueous dispersion containing the brightener is applied Heated to 60 ° C., a 3 g polypropylene fabric is placed in the solution, the temperature is increased to 95-98 ° C. within 10-15 minutes and left at this temperature for 30 minutes, and the fabric is then flown for 2 minutes since then, rinsed in cold water and then dried for 20 minutes at 60 C. - '. ''.

The fabric treated in this way shows a clear lightening effect.

If, instead of the above-mentioned brightener, the same amounts of a brightener of the formulas (1.2) ,, (^ 0), .od.e; r. (4 ?. ^s >, then similar effects are obtained with otherwise the same method of operation. - 3 0 983Ä / H3i

CIBA-GEIGY AG

Example 15

300 parts of hexamethylenediamine adipate are used in 300 parts dissolved in distilled water at 80 C. In this solution 1.8 parts of sebacic acid, 1.2 parts of titanium dioxide (anatase) and 0.3 parts of the optical brightener Formula (9) entered and stirred until a homogeneous distribution has taken place. The "liquid mixture is in the absence of oxygen in the at 150 ° Filled heated autoclave and then increased the temperature to 280 within an hour. While this time will be the. The pressure in the autoclave is kept below 30 atmospheres by blowing off steam. After reaching the temperature niaximuras of 280 the pressure was brought to atmospheric pressure within 10 to 20 minutes by blowing off the volatile components. The mass is then held at 280 for a further 4 hours at atmospheric pressure with the exclusion of oxygen. To During this time, the condensation has progressed so far that the polycondensate is replaced by an am The nozzle attached to the bottom of the autoclave can be spun. Pure white polyamide threads are obtained in this way.

Similar effects are obtained if you use otherwise same procedure, instead of the above-mentioned brightener, the same amounts of brightener of the formulas (12),

309834/1130

ciBA-GEiGYAG - 44 -.

(13), (14), (18), (29), (38), (40), (45) or (53) are used .

Example 16

400 parts of caprolactam, 40 parts of water, 0.4 parts of optical Aafheller of formula (18) and 1.6 parts Titanium dioxide (anatase) are mixed together and heated to 70 ° until the mass liquefies. the liquid mixture is poured into a pressure vessel made of stainless steel and with the exclusion of Oxygen heated to a temperature of 250 ° within one hour, with a pressure of 10-15 atmospheres occurs. After this time the water is distilled off and then the polymeric mass is kept pressureless at 250 ° for 3 hours for complete degassing. In doing so, dip mass reaches a viscosity which allows the polymer by means of nitrogen through a nozzle attached to the bottom of the pressure vessel in the form of ribbons or to squeeze out filaments. The solidified polyamide is made by extraction with water from monomeric fractions freed. The polyamide fiber made by this process is characterized by a very high degree of whiteness a, us.

If one proceeds as indicated in the above example, but instead of the brightener mentioned there, the same amounts are used

3098 34/1130

CJBA-GElGY AQ

. a brightener of the formulas (9), (12) ,. (13.), (29), (38), (AO), (45) or (53), similar effects are obtained with otherwise the same working method.

Example 17

1000 parts of polyester granules made from polyterephthalic acid ethylene glycol are intimately mixed with 0.25 parts of the optical brightener of formula (12) and then blended under nitrogen from an extruder at a temperature of 265 - 285 in known way spun into threads through a spinneret. The polyester threads obtained in this way are brilliant white aspect.

Proceed as indicated in the above example, but use the same brightener instead of the one mentioned there Quantities of a brightener of the formulas (9), (13), (17), (Au), (41), (45) or (53) are obtained with otherwise similar effects in the same way of working.

Example 18

In a stainless steel autoclave equipped with a stirrer, a gas inlet tube, a vacuum device, a descending cooler and a heating jacket, 388 g of benzene-1,4-dicarboxylic acid dimethyl ester,

309834/1130

CIBA-GEIGY AG

300 g of 1,2-ethanediol and 0.4 g of antimony oxide while blowing through heated by pure nitrogen to an outside temperature of 200 and kept at this temperature for 3 hours. In the process, methanol slowly distills off. Now are under 'exclusion of air 0.4 g of the optical brightener of the formula (12), dissolved in 40 g of 1,2-ethanediol, carefully in the autoclave smuggled in after keeping the temperature within a Hour has increased to 285 outside temperature, whereby 1,2-ethanediol distilled off. This is followed by the autoclave Vacuum applied, the pressure slowly reduced to 0.2 torr and the condensation was completed under these conditions for 3 hours. During these operations will well stirred. The liquid condensation polymer is then squeezed out with nitrogen through the floor nozzle. Monofilaments can be produced from the polymers obtained in this way, which show a brilliant white aspect.

If, instead of the abovementioned brightener, the same amounts of a brightener "of the formulas (" 9) _r (13), (17), (27), (40), (41), (45) or (53) are used, one obtains at otherwise the same working method, similar effects.

Example 19

In the kneader, there are 67 parts of polyvinyl chloride powder and 33 parts Dioctyl phthalate, 2 parts di-n-butyl-dilauryl-dioxystannate,

CLBA-GEiGY AG

0.3 part of sodium pentaoctyl triplyphosphate. with 0.05 Divide the optical brightener of the formula (45) on the Mixing roller mill gelatinized at 160 for 15 minutes and then drawn out into foils. The one produced in this way Polyvinyl chloride film shows strong fluorescence and a brilliant white aspect in daylight.

If the same brightener is used instead of the above Quantities of a brightener of the formulas (.9), (12), (13), (17), (33), (35), (45) or (46) are obtained with otherwise similar effects in the same way of working.

Example 20

In the kneader, 100 parts of polypropylene and 0.5 parts of titanium dioxide 0.05 parts of the optical brightener are added of the formula (9) homogenized at 200. The melt is under an inert gas of 2-3 atm and a temperature from 280 - 300 spun by known methods through spinnerets. Draw the polypropylene threads thus obtained is characterized by a high "degree of whiteness. If the same amounts of a brightener are used instead of the above-mentioned brightener of the formulas (12), (15), (31), (40) or (42), similar procedures are obtained with otherwise the same procedure Effects.

309834/1130

Claims (8)

Claims a) hydrogen b) alkyl of 2 to 18 carbon atoms c) 5 or 6 ring members containing cycloalkyl with 5 to 10 carbon atoms. ^. d) alkyl with 1 to 18 carbon atoms, substituted by hydroxy, alkoxy with 1 to 12 carbon atoms, optionally substituted with halogen, methyl or methoxy phenyl, carboxy, carbalkoxy with 2 to 13 carbon atoms, optionally on nitrogen with alkyl with 1 to 1-2 carbon atoms or phenyl substituted carbamoyl, an optionally quaternized one Heterocycles with 5 or 6 ring members, where 1 to 3 ring members represent nitrogen atoms, the 309834/1130 Sulpho group or its salts or optionally quaternized dialkylamine with 1 to 12 carbon atoms per alkyl part. e) optionally substituted with halogen, methyl or methoxy phenyl or f) an optionally quaternized heterocycle with 5 or 6 ring members, with 1 to 3 ring members representing nitrogen atoms, X and X ¹ independently of one another in 3 or. 3'-position alkoxy with 1 to 4 carbon atoms or halogen, Y and Y ¹ independently of one another in 6 or. 6'-position alkoxy with 1 to 4 carbon atoms, acj'loxy with 1 to 4 carbon atoms, benzoyloxy or halogen, t, u, ν and w independently of one another the number 1 or O and Z and Z ^f independently of one another are hydrogen or the sulfo group or their salts, 309834/1130 CiBA-GEIGYAG 2. 4,4'-Dinaphthyl-1,1 ', 8,8'-tetracarboxylic acid diimides ge mass claim 1, corresponding to the formula · 2 . 00 « R, and R 'independently of one another a) hydrogen ' b) alkyl of 2 to 18 carbon atoms c) Cyclohexyl which is optionally substituted by methyl d) optionally in the phenyl part with "halogen, methyl or Methoxy substituted Phenylalkyi with 1 to 4 carbon atoms in the alkyl part e) with hydroxy, alkoxy with 1 to 12 carbon atoms or the sulfo group-substituted alkyl with 2 to 4 Carbon atoms, f) with a radical -COZ., or -COH (Z ₂ Z ₃ ), where 2L hydroxyl or alkoxy rait 1 to 12 carbon atoms, Z «hydrogen, alkyl with 1 to 4 carbon atoms or phenyl and Z« hydrogen or alkyl with 1 to 4 · carbon atoms represent substituted alkyl CIBA-GEiGY AG 1 to 12 carbon atoms g) with an optionally quaternized dialkylamine radical with 1 to 4 carbon atoms per alkyl part substituted alkyl with 2 to 6 carbon atoms h) alkyl having 2 to 4 carbon atoms, substituted by morpholino optionally substituted by methyl, Piperazino, piperidino, imidazolidon-1-yl or optionally substituted in the 3-position by hydroxy or methoxy Pyridyl-2. or pyridyl-4, these being nitrogen-containing . '. Remnants, can be quaternized, i) optionally substituted with halogen, methyl or methoxy phenyl or k) optionally quaternized pyridyl-2, pyridyl-4 or l, 2,4-triazol-3-yl, X and X ¹ independently of one another in 3 or. 3'-position alkoxy with 1 to 4 carbon atoms or halogen, Y .. and Y ¹ independently of one another in 6 or. 6'-position alkoxy with 1 to 4 carbon atoms, acyloxy with 1 to 4 carbon atoms, benzoyloxy or halogen, t, u, ν and w are independently the number 1 or O Z and Z '. independently of one another are hydrogen or the sulfo group or their salts. 309834/1130 CIBA-GEIGYAG - SZ - 3. 4,4'-Dinaphthyl-1, -I ¹ , 8,8'-tetracarboxylic acid diimide according to claim 1, corresponding to the formula 3 (3) • where R _? a) hydrogen b) alkyl of 2 to 12 carbon atoms c) Cyclohexyl which is optionally substituted by methyl ' d) Phenylalkyl with 1 to 4 carbon atoms in the alkyl part e) with hydroxy, alkoxy with 1 to 4 carbon atoms, Carboxy, carbalkoxy with 2 to 5 carbon atoms, the Sulfo group or an optionally quaf; Dialkylamine radical with 1 to 4 carbon atoms each Alkyl radical substituted alkyl with 2 or 3 carbon atoms, f) optionally quaternized morpholine »-, piperazino-, Imidazolidon-1-yl-, pyridyl-2- or 3-hydroxypyridyl-2-ethyl g) methoxyphenyl or phenyl, or h) optionally quaternized P.yrid37l-2, pyridyl-4 or l, 2,4-triazol-3-yl,
X _{1 is} hydrogen or in the 3- or 6-position or 3'- or 3 0 9 8 3 4/1130 CIBA-GEIGY AQ 6'-position alkoxy with 1 to 4 carbon atoms or chlorine and Z is hydrogen or the sulfo group or its salts, mean. 309834/1130 CIBA-GEIGYAG - 4. 4,4 ^r -Dinapht: liyl-l, I ¹ , 8,8 '-tetracarboiisäurediimide according to claim 1, corresponding to the formula 4 (4) where R ^. - - a) Alkyl with 2 to 12 carbon atoms b) alkyl with 2 or 3 carbon atoms substituted by alkoxy with 1 to 4 carbon atoms, c) with Carbalkox} * - substituted with 2 to 5 carbon atoms -'- Alkyl with 1 to 11 carbon atoms, d) with dialkylamino with 1 to 4 carbon atoms per alkyl part substituted alkyl with 2 to 6 carbon atoms or. . _: e) pyridyl-2 or 3-hydroxypyridyl-2 and Χ-, hydrogen or in the 3- or 6-, or 3'- or δ'-position mean alkoxy with 1 to 4 carbon atoms or chlorine. 309834/1130 CIBA-GEIGY AG 5. Process for the preparation of 4,4'-dinaphthyl-l, l ', SjS'-tetracarboxylic diimides of the formula 1 (1) in which. R and R 'independently of one another a) hydrogen b) alkyl of 2 to 18 carbon atoms c) Cycloalkyl containing 5 or 6 ring members and having 5 to 10 carbon atoms ι ι ^: d) Alkyl with 1 to 18 carbon atoms, substituted with hydroxy, alkoxy with 1 to 12 carbon atoms, optionally with halogen, methyl or methoxy I substituted phenyl, carboxy, carbalkoxy with 2 to 13 ! Carbon atoms, optionally on nitrogen with alkyl having 1 to 12 carbon atoms or phenyl 'substituted carbamoyl, one optionally 'Quaternized heterocycle having 5 or 6 ring members, where 1 to 3 ring members represent nitrogen atoms, the sulfo group or its salts or optionally 309834/1 130 CIBA-GEIGY AG quaternized dialkylamine with 1 to 12 carbon; ::. :: ■ atoms per alkyl part
e) optionally with halogen, methyl or methoxy substituted phenyl or
f). an optionally quaternized heterocycle with 5 or 6 ring members, where 1 to 3 ring members represent nitrogen atoms, X and X ^1, independently of one another, in the 3 or 3 'position, alkoxy with 1 to 4 carbon atoms, or halogen, Y and Y 'independently of one another in 6 or. 6'-position ^: located alkoxy with 1 to 4 carbon atoms, acyloxy with 1 to 4 carbon atoms, benzoyloxy or halogen, t, u, ν and w are independently the number 1 or O and Z and Z 'are independently hydrogen or the sulfo group or their salts, characterized in that one mole of a compound of formula 5 O (5) 309834/1 130 ciBA-GEiGYAQ - 57 - wherein Y, Y ', X, X ¹ , t, u, ν and w have the meaning given, with one mole each of a compound of the formula 6a and 6b (6a) R-NH ₂ and R ^! -NH ₂ (6b) wherein R and R 'with the exception of the quaternizing groups have the meaning given, and the reaction product is optionally sulfonated and / or quaternized. 309834/1130 Annex to the entry of 26 * 4.1973 in "matters of patent application File number: P 23 06 399.2 - Gase 1-8027 / - Applicant: CIBA-GETGY AG, Basel - Ü.Ze-iehen: 22 039-BR / H 6. Use of the compounds according to Claims 1 to 4 for the optical brightening of organic materials, especially polycondensates, polyaddition products and Polymerization products. 7. Use according to claim 6, characterized in that
Polyamides, polyesters, polyacrylonitrile, cellulose acetates, polyvinyl chloride or polypropylene are lightened
will. 8. Use according to claim 6 or 7, characterized in that the optical brightener is incorporated or added to the materials in amounts of 0.0005 to 2%, preferably 0.005 to 0.5 %, based on the amount by weight of the material to be optically brightened applies these materials. 309834/1130